For someone whose big sister is a bikini queen, Ashlee Simpson is a little more reserved when it comes to sharing swimsuit photos than older sibling Jessica Simpson. But the singer still manages to slip into a sexy two-piece every now and then.
The proud mom of three and her husband, Evan Ross, have a backyard pool at their Los Angeles area mansion, but Ashlee isn’t one to post thirst trap pictures of herself in it. The couple prefer to share photos of their children, daughter Jagger Snow, born in 2015, and son Ziggy Blu, who came along in 2020, enjoying the water. Still, Ashlee has slipped on a swimsuit in pictures playing with her kids in the water on occasion. The singer also shares a teenage son, Bronx Wentz, with ex-husband Pete Wentz.
Ashlee and Evan definitely enjoy warm weather outings, be it a boating trip in Austin, Texas, or a vacation to Maui as a family. The “La La” singer showed off her incredible bikini body during a Caribbean outing in a photo while paddleboarding alongside one of her best girlfriends.
Evan, whose mom is iconic singer Diana Ross, is so proud of how great his significant other looks in swimwear. He shared a black-and-white photo to Instagram in 2016 of Ashlee posing in a pool wearing a plunging black one-piece with a large pineapple print on the front. “THATS MY WIFE!! @ashleesimpsonross,” he wrote in the caption, adding the hashtag, “mother of my child,” and adding: love love love love love pineapples.”
The couple married in a bohemian-themed ceremony at his mother’s Greenwich, Connecticut, estate on August 30, 2014. Diana officiated the pair’s wedding and later thrilled guests by performing her 1981 hit “Endless Love” at the reception.
The whole event was a family affair, as Ashlee’s sister, Jessica, served as matron of honor while her then-2-year-old daughter, Maxwell took on flower girl duties as the mogul’s then 14-month-old son Ace served as ring bearer. Ashlee’s then-5-year-old son Bronx accompanied his mom down the aisle to Evan.
Ashlee and Evan had been friends for more than a decade when things turned romantic in 2013, and after that things moved very quickly! Evan popped the question during Hawaiian vacation in 2014, and eight months later, they married. They’re still blissfully in love today.
Scroll down to see Ashlee’s best swimsuit photos.